Cheating a bit here, as the trail is really a collection of Boston's revolutionary sights, including a few others on this list. Leading 2.5 miles from Boston Common to the Bunker Hill Monument, the Freedom Trail is well marked and easy to follow as it traces the events leading up to and following the War of Independence.

America's oldest public park, Boston Common has a long and storied history, serving as a campground for British troops during the Revolutionary War and as green grass for cattle grazing until the 1830s. Nowadays, the Common is a place for picnicking and people-watching. In winter, the Frog Pond attracts ice-skaters, while summer draws theater lovers for Shakespeare on the Common. This is also the starting point for the Freedom Trail.

To protest against unfair taxes, a gang of rebellious colonists dumped 342 chests of tea into the water. The 1773 protest – the Boston Tea Party – set into motion the events leading to the Revolutionary War. Nowadays, replica Tea Party Ships are moored at Griffin's Wharf, alongside an excellent experiential museum dedicated to the catalytic event. Using re-enactments, multimedia and fun exhibits, the museum addresses all aspects of the Boston Tea Party and subsequent events.

Opposite the main entrance to Harvard Yard, Cambridge Common is the village green where General Washington took command of the Continental Army on July 3, 1775. Dawes Island at the south end pays tribute to William Dawes, the 'other rider', who on April 18, 1775 warned that the British were coming (look for the bronze hoofprints embedded in the sidewalk).

One of the oldest pubs in Boston, the Warren Tavern has been pouring pints for its customers since George Washington and Paul Revere drank here. It is named for General Joseph Warren, a fallen hero of the Battle of Bunker Hill (shortly after which – in 1780 – this pub was opened).

Directly in front of the Old State House, encircled by cobblestones, a bronze plaque marks the spot where the first blood was shed for the American independence movement. On March 5, 1770, an angry mob of colonists swarmed the British soldiers guarding the State House, hurling snowballs, rocks and insults. Thus provoked, the soldiers fired into the crowd and killed five townspeople, including Crispus Attucks, a former slave. The incident sparked enormous anti-British sentiment.

This 220ft granite obelisk monument commemorates the turning-point battle that was fought on the surrounding hillside on June 17, 1775. Ultimately, the Redcoats prevailed, but the victory was bittersweet, as they lost more than one-third of their deployed forces, while the colonists suffered relatively few casualties. Climb the 294 steps to the top of the monument to enjoy the panorama of the city, the harbor and the North Shore.

Brattle St’s most famous resident was Henry Wadsworth Longfellow, whose stately manor is now a National Historic Site. The poet lived here from 1837 to 1882, writing many of his most famous poems, including "Evangeline" and "The Song of Hiawatha." Incidentally, one reason Longfellow was so taken with this house was its historical significance. During the Revolutionary War, General Washington appropriated this beauty from its absent Loyalist owner and used it as his headquarters.

Forest Hills is a gorgeous, green cemetery that is filled with art and whimsy. It is still an active burial ground, but it also plays the role of open-air museum. The walking paths are lined with sculptures paying tribute to individuals and causes from times past, while a contemporary sculpture path winds its way around the historic gravestones, connecting then and now. The gravestones here include Revolutionary War heroes William Dawes and Joseph Warren.